2-Methoxyethylamine → HCID 69482053, compound

HRID 2364247Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31](OCC)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:37][O:38][CH2:39][CH2:40][NH2:41]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31]([NH:41][CH2:40][CH2:39][O:38][CH3:37])=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)(=[O:23])=[O:24])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(1-pyrrolidinylsulfonyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.0387 mmol) in ethanol (1 mL) was added 2-methoxyethylamine (40 μL, 0.460 mmol). The reaction mixture was heated in a microwave at 140° C. for 20 minutes. The reaction mixture was concentrated in vacuo. Purification by reverse phase HPLC provided 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1-[3-(1-pyrrolidinylsulfonyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.26 (s, 1H), 8.57 (s, 1 H), 7.75 (s, 1 H), 7.22 (dd, J=8.5, 5.4 Hz, 2 H), 7.02 (t, J=8.7 Hz, 2 H), 4.40 (t, J=8.0 Hz, 2 H), 4.13 (s, 2 H), 3.66 (q, J=5.1 Hz, 2 H), 3.59 (m, 2 H), 3.42 (s, 3 H), 3.37-3.34 (m, 4 H), 3.05 (t, J=6.6 Hz, 2 H), 2.18 (m, 2 H), 1.97-1.93 (m, 4 H); HRMS C26H31FN4O6S (M+H)+ calcd 547.1948, found 547.2009.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customPurification by reverse phase HPLC

Sources & evidence

ORD record: ord-86fa3a6c9c504b2d8032a5debdc069e4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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